Potassium Phosphate, Tribasic → HCID 90415003, compound

HRID 1522011Notes

Reaction equation

HRID 1522011 reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[NH:9][C:10]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)=[CH:11][C:3]=12.[F:25][C:26]1[CH:27]=[CH:28][C:29]([O:35][CH3:36])=[C:30](B(O)O)[CH:31]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.O>[F:8][C:7]1[C:2]([C:28]2[CH:27]=[C:26]([F:25])[CH:31]=[CH:30][C:29]=2[O:35][CH3:36])=[C:3]2[CH:11]=[C:10]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[NH:9][C:4]2=[N:5][CH:6]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 90413169HCID 90413169, compound

Product 1

HCID 90415003HCID 90415003, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of Example 255B (600 mg, 1.696 mmol), (5-fluoro-2-methoxyphenyl)boronic acid (403 mg, 2.374 mmol), phenylallylchloro[1,3-bis(diisopropylphenyl)-2-imidazol-2-ylidene]palladium(II) (110 mg, 0.170 mmol), and potassium phosphate (1080 mg, 5.09 mmol) in 12 mL tetrahydrofuran and 3 mL water was degassed with nitrogen and heated in a Biotage microwave for 40 minutes at 120° C. The mixture was extracted with ethyl acetate and purified by silica gel column chromatography eluting with 0-5% methanol in dichloromethane to afford the title compound. MS (ESI(+)) m/e 444 (M+H)+.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. custompurified by silica gel column chromatography
  3. washeluting with 0-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-7416d0e0a4db4a899066288ddcba4175
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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